- Effects of ferrocenyl 4-(Imino)-1,4-dihydroquinolines on xenopus laevis prophase i-arrested oocytes: Survival and hormonal-induced m-phase entry
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Xenopus oocytes were used as cellular and molecular sentinels to assess the effects of a new class of organometallic compounds called ferrocenyl dihydroquinolines that have been developed as potential anti-cancer agents. One ferrocenyl dihydroquinoline co
- Bodart, Jean-Fran?ois,Bousquet, Till,Cailliau, Katia,Lescuyer, Arlette,Marchand, Guillaume,Marin, Matthieu,Markey, Angel,Martoriati, Alain,Molinaro, Caroline,Pelinski, Lydie,Pellegrini, Sylvain,Wambang, Nathalie
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- Palladium-catalyzed regioselective aerobic oxidative cyclization via C-H activation in chloroquine analogues: Synthesis and cytotoxic study
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The intramolecular regioselective aerobic oxidative cyclization via two types of discrete C-H activation in 7-chloroquinoline analogues is described. All the synthesized compounds are screened against three human cancer cell lines (CCRF-CEM, HT29, and MCF
- Senthil Kumar, Gopal,Ali, Mohamed Ashraf,Choon, Tan Soo,Rajendra Prasad, Karnam Jayarampillai
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- Synthesis method of aza-arylamine compound and aza-arylamine compound
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The invention provides a synthesis method of an aza-arylamine compound as shown in a formula (I). The synthesis method comprises the following steps: an aza aromatic hydrocarbon compound as shown in aformula (II) reacts with an amine compound as shown in a formula (III) in presence of alkali and under a heating condition, so that u X substituent groups on an A ring of the compound as shown in theformula (II) are substituted by NRR in the compound as shown in the formula (III), and the compound as shown in the formula (I) is obtained, wherein A is an aza six-membered aromatic ring or five-membered aromatic ring, and is an independent single ring or is fused with a ring B; X refers to that the A ring has at least n X substituent groups, each X substituent group is independently selected from the group consisting of F, Cl, Br, I, CN, alkoxy of C and alkylthio of C, and n is a positive integer selected from 1-5; and the alkali is one or a mixture of more selected fromof BuOK, BuONa, BuONa, KHMDS, NaHMDS and LiHMDS. The synthesis method provided by the invention does not need the use of transition metal catalysts, is simple and convenient to operate, is economical and practical and is environmentally friendly. In addition, the invention also provides the aza-arylamine compound prepared by the method.
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Paragraph 0059; 0060; 0061; 0092
(2019/04/26)
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- Anticancer-Active N-Heteroaryl Amines Syntheses: Nucleophilic Amination of N-Heteroaryl Alkyl Ethers with Amines
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A mild amination protocol of N-heteroaryl alkyl ethers with various amines is described. This transformation is achieved by utilizing simple and readily available base as promoter via C-O bond cleavage, offering a new amination strategy to access several anticancer-active compounds. This work is highlighted by the excellent functional group compatibility, scalability, wide substrate scope, and easy derivatization of a variety of drugs.
- Wang, Xia,Yang, Qiu-Xia,Long, Cheng-Yu,Tan, Yan,Qu, Yi-Xin,Su, Min-Hui,Huang, Si-Jie,Tan, Weihong,Wang, Xue-Qiang
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supporting information
p. 5111 - 5115
(2019/07/03)
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- Functionalized acridin-9-yl phenylamines protected neuronal HT22 cells from glutamate-induced cell death by reducing intracellular levels of free radical species
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The in vitro neuronal cell death model based on the HT22 mouse hippocampal cell model is a convenient means of identifying compounds that protect against oxidative glutamate toxicity which plays a role in the development of certain neurodegenerative diseases. Functionalized acridin-9-yl-phenylamines were found to protect HT22 cells from glutamate challenge at submicromolar concentrations. The Aryl1-NHAryl2 scaffold that is embedded in these compounds was the minimal pharmacophore for activity. Mechanistically, protection against the endogenous oxidative stress generated by glutamate did not involve up-regulation of glutathione levels but attenuation of the late stage increases in mitochondrial ROS and intracellular calcium levels. The NH residue in the pharmacophore played a crucial role in this regard as seen from the loss of neuroprotection when it was structurally modified or replaced. That the same NH was essential for radical scavenging in cell-free and cell-based systems pointed to an antioxidant basis for the neuroprotective activities of these compounds.
- Nguyen, Thuy,Yang, Tianming,Go, Mei-Lin
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supporting information
p. 1830 - 1838
(2015/03/14)
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- Trifluoroacetic acid in 2,2,2-trifluoroethanol facilitates SNAr reactions of heterocycles with arylamines
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Small-molecule drug discovery requires reliable synthetic methods for attaching amino compounds to heterocyclic scaffolds. Trifluoroacetic acid-2,2,2-trifluoroethanol (TFA-TFE) is as an effective combination for achieving SNAr reactions between
- Carbain, Benoit,Coxon, Christopher R.,Lebraud, Honorine,Elliott, Kristopher J.,Matheson, Christopher J.,Meschini, Elisa,Roberts, Amy R.,Turner, David M.,Wong, Christopher,Cano, Celine,Griffin, Roger J.,Hardcastle, Ian R.,Golding, Bernard T.
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supporting information
p. 2311 - 2317
(2014/03/21)
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- Functionalized acridin-9-yl phenylamines protected neuronal HT22 cells from glutamate-induced cell death by reducing intracellular levels of free radical species
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The in vitro neuronal cell death model based on the HT22 mouse hippocampal cell model is a convenient means of identifying compounds that protect against oxidative glutamate toxicity which plays a role in the development of certain neurodegenerative diseases. Functionalized acridin-9-yl-phenylamines were found to protect HT22 cells from glutamate challenge at submicromolar concentrations. The Aryl1-NH-Aryl2 scaffold that is embedded in these compounds was the minimal pharmacophore for activity. Mechanistically, protection against the endogenous oxidative stress generated by glutamate did not involve up-regulation of glutathione levels but attenuation of the late stage increases in mitochondrial ROS and intracellular calcium levels. The NH residue in the pharmacophore played a crucial role in this regard as seen from the loss of neuroprotection when it was structurally modified or replaced. That the same NH was essential for radical scavenging in cell-free and cell-based systems pointed to an antioxidant basis for the neuroprotective activities of these compounds.
- Nguyen, Thuy,Yang, Tianming,Go, Mei-Lin
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supporting information
p. 1830 - 1838
(2014/04/17)
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- Structural optimization of quinolon-4(1 H)-imines as dual-stage antimalarials: Toward increased potency and metabolic stability
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Discovery of novel effective and safe antimalarials has been traditionally focused on targeting erythrocytic parasite stages that cause clinical symptoms. However, elimination of malaria parasites from the human population will be facilitated by intervent
- Ressurrei??o, Ana S.,Gon?alves, Daniel,Sitoe, Ana R.,Albuquerque, Ine?s S.,Gut, Jiri,Góis, Ana,Gon?alves, Lídia M.,Bronze, Maria R.,Hanscheid, Thomas,Biagini, Giancarlo A.,Rosenthal, Philip J.,Prude?ncio, Miguel,O'Neill, Paul,Mota, Maria M.,Lopes, Francisca,Moreira, Rui
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supporting information
p. 7679 - 7690
(2013/11/06)
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- Quinolines derivatives as novel sunscreening agents
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Currently, the research and development of sunscreens play an important role on the synthesis of actives that are stable in various kinds of formulations - in addition to their efficiency and broad spectrum of protection against ultraviolet radiation. Our
- Polonini, Hudson C.,Dias, Rafael M.P.,Souza, Isabela O.,Gon?alves, Karla Mara,Gomes, Tiago B.B.,Raposo, Nádia R.B.,Da Silva, Adilson David
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p. 4506 - 4510
(2013/08/23)
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- Microwave-accelerated solvent- and catalyst-free synthesis of 4-aminoaryl/alkyl-7-chloroquinolines and 2-aminoaryl/alkylbenzothiazoles
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An efficient synthesis of 4-aminoaryl/alkyl-7-chloroquinolines and 2-aminoaryl/alkylbenzothiazoles has been developed by microwave-accelerated regioselective aromatic nucleophilic substitution of 4,7-dichloroquinoline and 2-chlorobenzothiazole with aromatic and aliphatic amines under solvent-free conditions in the absence of any added protic or Lewis acid catalyst. Chemoselective reaction with the amino group in preference to the phenolic hydroxy group was observed. Thus, the treatment of 4,7-dichloroquinoline (1 equiv.) with a mixture of aniline (2 equiv.) and phenol (2 equiv.) afforded exclusive formation of 4-aminophenyl-7-chloroquinoline. When 4,7-dichloroquinoline (1 equiv.) was separately treated with 2-aminophenol (2 equiv.) and 4-aminophenol (2 equiv.), 4-(2'-hydroxyphenyl)-7-chloroquinoline and 4-(4'-hydroxyphenyl)-7-chloroquinoline, respectively, were formed. CSIRO 2007.
- Motiwala, Hashim F.,Kumar, Raj,Chakraborti, Asit K.
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p. 369 - 374
(2008/02/11)
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